methyl 3-O-benzyl-4-O-(3-O-benzyl-2,6-dideoxy-β-D-arabino-hexopyranosyl)-2,6-dideoxy-α-D-arabino-hexopyranoside | 153596-70-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 3-O-benzyl-4-O-(3-O-benzyl-2,6-dideoxy-β-D-arabino-hexopyranosyl)-2,6-dideoxy-α-D-arabino-hexopyranoside
• 英文别名: methyl 3-O-benzyl-4-O-(3-O-benzyl-6-deoxy-β-D-arabino-hexopyranosyl)-2,6-dideoxy-α-D-arabino-hexopyranoside
• CAS: 153596-70-4
• 化学式: C₂₇H₃₆O₇
• 分子量: 472.579
• InChiKey: DVOVCIZKTSEPCB-HQDVQZMQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.82
• 重原子数：
  34.0
• 可旋转键数：
  9.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  75.61
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  methyl 3-O-benzyl-4-O-(3-O-benzyl-2,6-dideoxy-β-D-arabino-hexopyranosyl)-2,6-dideoxy-α-D-arabino-hexopyranoside 在 三乙基硅烷 、 碘 、 sodium amide 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 8.0h， 生成 methyl 3-O-benzyl-4-O-(3-O-benzyl-4-O-(3-O-benzyl-4-O-(3-O-benzyl-2,6-dideoxy-β-D-arabinohexopyranosyl)-2,6-dideoxy-β-D-arabino-hexopyranosyl)-2,6-dideoxy-β-D-arabino-hexopyranosyl)-2,6-dideoxy-α-D-arabino-hexopyranoside
  参考文献：
  名称：

  β-连接的2,6-脱氧寡糖的直接和立体选择性合成。

  摘要：

  DOI：

  10.1002/anie.200604031
• 作为产物：
  描述：

  (2R,3S,4R,6S)-6-Methoxy-2-methyl-tetrahydro-pyran-3,4-diol 在 三乙基硅烷 、 碘 、 二正丁基氧化锡 、 sodium amide 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 19.5h， 生成 methyl 3-O-benzyl-4-O-(3-O-benzyl-2,6-dideoxy-β-D-arabino-hexopyranosyl)-2,6-dideoxy-α-D-arabino-hexopyranoside
  参考文献：
  名称：

  β-连接的2,6-脱氧寡糖的直接和立体选择性合成。

  摘要：

  DOI：

  10.1002/anie.200604031

文献信息

• Efficient Synthesis of the Deoxysugar Part of Versipelostatin by Direct and Stereoselective Glycosylation and Revision of the Structure of the Trisaccharide Unit
  作者：Hiroshi Tanaka、Atsushi Yoshizawa、Shuhei Chijiwa、Jun-ya Ueda、Motoki Takagi、Kazuo Shin-ya、Takashi Takahashi

  DOI：10.1002/asia.200800448

  日期：2009.7.6

  Sweets for my sweet! Efficient synthesis of the deoxysugar part of versipelostatin (VST) was achieved by direct and stereoselective glycosidation of the reduced VST aglycon. Comparison of the synthetic and natural VST products using NMR indicate that VST has a β‐d‐digitoxose‐(1,4)‐α‐l‐oleandrose‐(1,4)‐β‐d‐digitoxose trisaccharide. A biological assay indicates that the deoxyoligosaccharide unit of the

  糖果给我带来甜蜜！通过减少的VST糖苷配基的直接和立体选择性糖苷化，可实现VersipeloSTatin（VST）的脱氧糖部分的有效合成。使用NMR对合成和天然VST产品进行的比较表明，VST具有一个β-d-地氧糖-（1,4）-α-l-oleandrose-（1,4）-β-d-地氧糖三糖。生物学测定表明，合成糖苷的脱氧寡糖单元对于生物学活性很重要。
• Synthesis of a terminal A-B-C disaccharide fragment of flambamycin, curamycin, and avilamycin
  作者：Cyrill Žagar、Hans-Dieter Scharf

  DOI：10.1016/0008-6215(93)84119-q

  日期：1993.10

  Methyl 2,6-dideoxy-4-O-[2,6-dideoxy-4-O-(3,5-dichloro-4-hydroxy-2-methoxy-6-methylbenzoyl)-beta-D-arabino-hexopyranosyl]-alpha-D-arabino-hexopyranoside (25) corresponds to an A-B-C disaccharide subunit of the title antibiotics. It was synthesized from suitably protected monosaccharide and aromatic precursors. The readily available 4,6-O-benzylidene-1,2-O-(R)-propylidene-alpha-D-glucopyranose was converted in six steps into 2-O-acetyl-4-O-benzoyl-3-O-benzyl-6-deoxy-alpha-D-glucopyranosyl bromide, which was condensed with methyl 3-O-benzyl-2,6-dideoxy-alpha-D-arabino-hexopyranoside in the presence of mercury(II) cyanide. Methyl 4-O-(2-O-acetyl-4-O-benzoyl-3-O-benzyl-6-deoxy-beta-D-glucopyranosyl)-3-O-benzyl-2,6-dideoxy-alpha-D-arabino-hexopyranoside was converted either into methyl 2,6-dideoxy-4-O-(6-deoxy-beta-D-glucopyranosyl)-alpha-D-arabino-hexopyranoside by removal of the protective groups or into methyl 3-O-benzyl-4-O-(3-O-benzyl-2,6-dideoxy-beta-D-arabino-hexopyranosyl)-2,6-dideoxy-alpha-D-arabino-hexopyranoside (22) by selective deacetylation, Barton deoxygenation, and Zemplen debenzoylation. Disaccharide 22 was deprotonated with butyllithium and treated with 4-benzyloxy-3,5-dichloro-2-methoxy-6-methylbenzoyl chloride to give the title compound 25 after hydrogenolysis.